美国专利原文Word格式文档下载.docx
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andgoodthermal,adhesive,andelectricalproperties.Imidazoles,particularlyalkylatedimidazoles,areepoxycuringcatalystsknowntoprovidehighthermalstabilityepoxieswithexcellentproperties.However,epoxyresinformulationsthatutilizeconventionalalkylatedimidazoleshaveshortpotlivesanddonotprovidesufficientlatencyformanyapplications,suchasadhesiveandelectricalencapsulationapplications.Inaddition,conventionalimidazoleoralkylatedimidazolecuringcatalyststypicallyonlyprovideastandardglasstransitiontemperaturelowerthan150°
C.whenusedtocureconventionalbisphenolAepoxyresins.Thisisinsufficientforapplicationswhereahighglasstransitiontemperatureisdesirable,includingelectricaldeviceapplications,suchaselectricallaminates,flipchippackagingandelectricalencapsulation.
SUMMARY
Thepresentdisclosureisdirectedtophosphazeneblockedazolecompoundsandapplicationthereofinepoxyresins,methodsofproducingsame,andarticlescontainingsame.
Thepresentdisclosureprovidesacomposition.Inanembodiment,acompositionisprovidedandincludesacuringcatalyst,anepoxyresin,andanepoxyhardener.Thecuringcatalystincludesaphosphazeneblockedazolecompound(PBAC).Inafurtherembodiment,thePBACishexa(imidazolyl)cyclotriphosphazene.
Thepresentdisclosureprovidesanothercomposition.Inanembodimentacompositionisprovidedandincludesanepoxyresincuredwithacuringcatalystcomprisingaphosphazeneblockedazolecompound,andoptionallyanepoxyhardener.Inotherwords,thecompositionisthereactionproductofanepoxyresin,aPBAC,andoptionallyanepoxyhardener.Inafurtherembodiment,thePBACishexa(imidazolyl)cyclotriphosphazene.
Thepresentdisclosureprovidesamethod.Inanembodiment,amethodformakingacuredepoxyresinisprovidedandincludesmixingacuringcatalystcomprisingaphosphazeneblockedazolecompoundwithanepoxyresinandoptionallyanepoxyhardener.Themethodalsoincludesexposingthemixturetoatemperatureabovethecuringonsettemperature,wherebytheepoxyhardenerreactswiththeepoxyresininthepresenceofthecuringcatalysttoprovideacuredepoxyresin.
Thepresentdisclosureprovidesanarticle.Inanembodiment,anarticleisprovidedandincludesanepoxyresinandaphosphazeneblockedazolecompoundand/orthereactionproductofanepoxyresin,aphosphazeneblockedazolecompound,andoptionallyanepoxyhardener.Thearticlemaybeapre-preg,alaminate,anelectricallaminate,andcombinationsthereof.
Theepoxycompositionsofthepresentdisclosureexhibitimprovedlatency,and/orhigherglasstransitiontemperature,and/orafastercureratecomparedthanconventionalepoxyresinsandepoxyresinscuredwithimidazole-basedcuringcatalystsinparticular.
DETAILEDDESCRIPTION
Thepresentdisclosurerelatestotheuseofphosphazeneblockedazolecompounds(PBAC)ascuringcatalystsforepoxyresins.Inanembodiment,acompositionisprovided.Thecompositionincludesacuringcatalyst,anepoxyresin,andanepoxyhardener.Thecuringcatalystincludesaphosphazeneblockedazolecompound.
CuringCatalysts
Thecuringcatalystofthepresentcompositionincludesaphosphazeneblockedazolecompound.TheazolemoietyofthePBAC,canbesubstitutedorunsubstituted,andfacilitatestheformationofaninfusiblereactionproductbetweentheepoxyhardenerandtheepoxyresininafinalarticleofmanufacture,suchasastructuralcompositeorlaminate.Byaninfusiblereactionproduct,itismeantthattheepoxyresinhasessentiallycompletelycured,whichcanbeconsideredtobethepointduringthecuringprocessbeyondwhichthereisnochangebetweentwoconsecutiveTgmeasurements(ΔTg).
Theterm“phosphazene,”asusedherein,isachainmolecule,aringmoleculeorabridgedmoleculethatcontainsalternatingphosphorusandnitrogenatomswithtwosubstituentsoneachphosphorusatomandrepresentedbythestructure(I)below.
Thesubstituent(—R)maybethesameordifferentandmaybeahydrocarbylgroup,asubstitutedhydrocarbylgroup,aheteroatom,andcombinationsthereof.Thetermn′hasavalueof2to15,000.
Acyclicphosphazeneisrepresentedbythestructure(II)below.
1Rand2Rofstructure(II)maybethesameordifferentandmaybeanysubstituentrepresentedbyRforstructure(I).Thetermmisavaluefrom3toabout15.Anonlimitingexampleofasuitablecyclicphosphazeneiscyclotriphosphazenerepresentedbystructure(III)below.
The—Rsubstituentofstructure(III)maybeanyRsubstituentasinstructure(I)above.
Abridgedphosphazenehasthestructure(IV)below.
R3isabi-functionalamineoradiol.The—Rsubstituentsofstructure(IV)maybethesameordifferentandmaybeanyRsubstituentasinstructure(I).Thetermn′hasavalueof2to15,000.
Anyoftheforegoingphosphazenecompoundsofstructure(I)-(IV)maybeaphosphazeneblockedazolecompound(PBAC).An“azole,”“azolecompound,”or“azolegroup”asusedherein,isafive-memberedheterocyclicringstructurecontainingatleastonecarbonatomandatleastonenitrogenatom.Theazolemayormaynotbearomaticandmayormaynotbesubstituted.Theazolemayincludemorethanoneheteroatomand/ormorethanonenitrogenatom.Nonlimitingexamplesofsuitableazolecompoundsincludeimidazole,pyrazole,andtriazole,anyofwhichmayormaynotbesubstituted.
A“phosphazeneblockedazolecompound”isaphosphazenecompoundwhereineachsubstituentisanazolegroup.Nonlimitingexamplesofaphosphazeneblockedazolecompoundincludethephosphazeneofstructure(I),(II),(III)and/or(IV)whereineach—Rsubstituentisanazolegroup.
Acyclophosphazeneblockedazolecompoundcanbeobtainedthroughthereactionbetweencyclochlorophosphazeneandsubstituted/unsubstitutedimidazoles,triazolesorpyrazoleswithtertiaryamineasacidscavenger.Linearphosphazeneblockedazolecompoundcanbeobtainedthroughthereactionbetweenlinearchlorophosphazeneandsubstituted/unsubstitutedimidazoles,triazolesorpyrazoleswithtertiaryamineasacidscavenger.SuchreactionsaredescribedinCarriedo,GabinoA,“Phosphazenes”OrganophosphorusChemistry(2009),38332-386.
Abridgedcyclotriphosphazeneblockedazolecompoundcanbeobtainedthroughtwostepreactions:
firstly,cyclochlorotriphosphazenereactswithdiamineordioltopreparebridgedcyclochlorophosphazene;
thenthebridgedcyclochlorophosphazenecanreactwithsubstituted/unsubstitutedimidazoles,triazolesorpyrazolestopreparebridgedcyclotriphosphazene-blockedsubstitutedimidazoles,triazolesorpyrazoles.SuchreactionsaredescribedinBrandt,Krystyna,“Synthesisandpropertiesofthenewreactiveoligomerscontainingcyclophosphazenemoieties”,ChemiaStosowana(1986),30
(2),255-71.
Inanembodiment,thephosphazeneblockedazolecompoundisrepresentedbystructure(V-1)and/orthestructure(V-2)below.
Asshowninstructure(V-1),eachphosphazenesubstituentisanimidazolegroup.Structure(V-1)representshexa(imidazolyl)cyclotriphosphazene.Asshowninstructure(V-2),eachsubstituentmaybeasubstitutedimidazolegroupwhereinthesubstituent—Rofstructure(V-2)isthesameordifferentandisselectedfromhydrogen,aC1-C5hydrocarbylgroup,aC3-C5hydroxyalkylgroup,aC3-C4alkenylgroup,acyclohexylgroup,aC6-C10arylgroup,aC7-C8aralkylgroup,acyclicstructure,andcombinationsthereof.
Inanembodiment,thephosphazeneblockedazolecompoundisrepresentedbythestructure(VI)below.
Asshowninstructure(VI),eachphosphazenesubstituentisasubstitutedpyrazolegroup.Thesubstituent—Rofstructure(VI)isthesameordifferentandisselectedfromhydrogen,aC1-C5hydrocarbylgroup,aC3-C5hydroxyalkylgroup,aC3-C4alkenylgroup,acyclohexylgroup,aC6-C10arylgroup,aC7-C8aralkylgroup,acyclicstructure,andcombinationsthereof.
Inanembodiment,thephosphazeneblockedazolecompoundisrepresentedbythestructure(VII-1)and/orthestructure(VII-2)below.
Asshowninstructure(VII-1)andstructure(VII-2),eachphosphazenesubstituentisasubstitutedtriazolegroup.Thesubstituent—Rofstructure(VII-1)and/orstructure(VII-2)isthesameordifferentandisselectedfromhydrogen,aC1-C5hydrocarbylgroup,aC3-C5hydroxyalkylgroup,aC3-C4alkenylgroup,acyclohexylgroup,aC6-C10arylgroup,aC7-C8aralkylgroup,acyclicstructure,andcombinationsthereof.
Inanembodiment,thephosphazeneblockedazolecompoundisrepresentedbythestructure(VIII)below.
Thesubstituent—Rofstructure(VIII)isthesameordifferentandisselectedfromhydrogen,aC1-C5hydrocarbylgroup,aC3-C5hydroxyalkylgroup,aC3-C4alkenylgroup,acyclohexylgroup,aC6-C10arylgroup,aC7-C8aralkylgroup,acyclicstructure,andcombinationsthereof.
Inanembodiment,thephosphazeneblockedazolecompoundisrepresentedbythestructure(IX)below.
Structure(IX)isabridgedcyclophosphazenecompound.R3isabi-functionalamineoradiol.Thesubstituent—Rofstructure(IX)isthesameordifferentandisselectedfromhydrogen,aC1-C5hydrocarbylgroup,aC3-C5hydroxyalkylgroup,aC3-C4alkenylgroup,acyclohexylgroup,aC6-C10arylgroup,aC7-C8aralkylgroup,acyclicstructure,andcombinationsthereof.
Thecuringcatalystinthepresentcompositionactsasaneffectivecuringcatalystandprovidessubstantiallatencytothecomposition.Inadditionthecuringcatalystprovidesforfastcureattemperatures